Robert Redford: Ben Braddock, The Graduate
This classic coming-of-age tale starring Dustin Hoffman almost featured Robert Redford in the title role, but he was apparently just too cool.
"I said, 'You can’t play it. You can never play a loser.' And Redford said, 'What do you mean? Of course I can play a loser,'" reflected director Mike Nichols at a 2003 event, as recounted by Vanity Fair. "And I said, 'O.K., have you ever struck out with a girl?' and he said, 'What do you mean?' And he wasn’t joking."